2-p-Tolylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 350793-49-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-p-Tolylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 2-(tosyloxy)ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；(2-p-Toluolsulfonyloxy-ethyl)-tetra-O-acetyl-β-D-glucopyranosid；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-(4-methylphenyl)sulfonyloxyethoxy]oxan-2-yl]methyl acetate
• CAS: 350793-49-6
• 化学式: C₂₃H₃₀O₁₃S
• 分子量: 546.549
• InChiKey: ZDAGAJVZPVFZLB-XNBWIAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  175
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-p-Tolylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 Lindlar's catalyst sodium azide 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 34.0h， 生成 [2-(iminodiacetato)ethyl]-β-D-glucopyranoside
  参考文献：
  名称：

  用于过渡金属络合的葡萄糖和 2-脱氧葡萄糖的衍生化：与有机金属 99mTc 和 Re 前体的取代反应和基础 NMR 研究

  摘要：

  报道了葡萄糖和 2-脱氧葡萄糖在 C-1 位进行双功能化以实现过渡金属配位的合成策略。特别是合成和研究了可能用于诊断核医学的有机金属锝和铼配合物。具体而言，常见的亚氨基二乙酸 (IDA) 部分通过乙烯间隔基团 O-糖苷连接，以产生纯的 α-（在 2-脱氧葡萄糖的情况下）和 β-端基异构体（在葡萄糖的情况下）。糖衍生物与有机金属前体 [M(H2O)3(CO)3]+ (M = 99mTc, Re) 的反应以高产率产生了水溶性和水稳定性的单一产品。金属前体的三个水分子的置换以及金属-三羰基核的三齿配位仅通过胺和 IDA 螯合物的两个羧酸官能团通过 1D 和 2D 1H NMR 光谱、质谱法验证, 和红外光谱。放射性标记的产品 (99mTc) 在生理磷酸盐缓冲液 (pH = 7.4) 和人血浆中在 37 摄氏度的 24 小时内证明了它们在体外具有出色的稳定性。

  DOI：

  10.1002/1521-3765(20010504)7:9<1868::aid-chem1868>3.0.co;2-h
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 吡啶 、 3 A molecular sieve 、 mercury dibromide 作用下， 以 二氯甲烷 为溶剂， 生成 2-p-Tolylsulfonyloxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  用于过渡金属络合的葡萄糖和 2-脱氧葡萄糖的衍生化：与有机金属 99mTc 和 Re 前体的取代反应和基础 NMR 研究

  摘要：

  报道了葡萄糖和 2-脱氧葡萄糖在 C-1 位进行双功能化以实现过渡金属配位的合成策略。特别是合成和研究了可能用于诊断核医学的有机金属锝和铼配合物。具体而言，常见的亚氨基二乙酸 (IDA) 部分通过乙烯间隔基团 O-糖苷连接，以产生纯的 α-（在 2-脱氧葡萄糖的情况下）和 β-端基异构体（在葡萄糖的情况下）。糖衍生物与有机金属前体 [M(H2O)3(CO)3]+ (M = 99mTc, Re) 的反应以高产率产生了水溶性和水稳定性的单一产品。金属前体的三个水分子的置换以及金属-三羰基核的三齿配位仅通过胺和 IDA 螯合物的两个羧酸官能团通过 1D 和 2D 1H NMR 光谱、质谱法验证, 和红外光谱。放射性标记的产品 (99mTc) 在生理磷酸盐缓冲液 (pH = 7.4) 和人血浆中在 37 摄氏度的 24 小时内证明了它们在体外具有出色的稳定性。

  DOI：

  10.1002/1521-3765(20010504)7:9<1868::aid-chem1868>3.0.co;2-h

文献信息

• The synthesis of new fluorinated or nonfluorinated sugar phosphonates and phosphoramidates as building blocks in the synthesis of modified hyaluronic acid subunits
  作者：Katarzyna Koroniak-Szejn、Joanna Tomaszewska、Henryk Koroniak

  DOI：10.1080/10426507.2017.1311332

  日期：2017.6.3

  ABSTRACT ABSTRACT The synthesis of several new fluorinated or nonfluorinated sugar phosphonates and phosphoramidates as building blocks for the synthesis of modified hyaluronic acid subunits is described. These compounds were prepared from d-glucose and d-glucosamine hydrochloride. The syntheses of phosphonates and phosphoramidates are based on arbuzov and staudinger reactions. The products were fully

  图形摘要 摘要 描述了几种新的氟化或非氟化糖膦酸酯和氨基磷酸酯的合成，作为合成修饰透明质酸亚基的结构单元。这些化合物由 d-葡萄糖和 d-氨基葡萄糖盐酸盐制备。膦酸酯和氨基磷酸酯的合成基于 arbuzov 和 staudinger 反应。产物通过 1H、13C、19F、31P NMR 和 ESI MS 光谱进行了全面表征。
• Expeditious Synthesis of Glycosylated Phthalocyanines
  作者：Thomas Ziegler、Xavier Álvarez-Micó、Mario Calvete、Michael Hanack

  DOI：10.1055/s-2007-983753

  日期：——

  3,4-Dicyanophenyl O- and S-glycosides in the gluco, galacto, lacto, and cellobiose series were prepared in virtually quantitative yield through nucleophilic aromatic substitution of 4-nitrophthalonitrile with acetyl-protected glycoses and 1-thio-glycoses. Similarly, 2-(3,4-dicyanophenoxy)ethyl 2,3,4,6-tetra-O-acetyl-β-d-gluco- and galacto-pyranosides were obtained by nucleophilic substitution of 2-(tosyloxy)ethyl 2,3,4,6-tetra-O-acetyl-β-d-gluco- and -galactopyranoside with 3,4-dicyanophenol in 82% and 94% yields, respectively. All glycosides were deacetylated and tetramerized to the corresponding glycosylated zinc(II) phthalocyanines without further purification using a template condensation in 42-54% yields.

  在几乎定量的产率下，通过4-硝基邻苯二甲腈与乙酰保护的糖和1-硫糖进行亲核芳香取代反应，制备了3,4-二氰基苯基O-和S-糖苷，涉及葡萄糖、半乳糖、乳糖和纤维二糖系列。类似地，通过用3,4-二氰基酚对2-(托烯基氧)乙基2,3,4,6-四-O-乙酰-β-D-葡萄糖和-半乳糖吡喃糖进行亲核取代反应，分别获得了2-(3,4-二氰基苯氧)乙基2,3,4,6-四-O-乙酰-β-D-葡萄糖和-半乳糖的产物，产率为82%和94%。所有糖苷在未经进一步纯化的情况下，通过模板缩合法进行去乙酰化和四聚化，得到相应的糖苷化锌(II)酞菁，产率为42-54%。
• Biological evaluation of glucose and deoxyglucose derivatives radiolabeled with [99mTc(CO)3(H2O)3]+ core as potential melanoma imaging agents
  作者：Rosina Dapueto、Romina Castelli、Marcelo Fernández、José A. Chabalgoity、María Moreno、Juan Pablo Gambini、Pablo Cabral、Williams Porcal

  DOI：10.1016/j.bmcl.2011.09.106

  日期：2011.12

  Glucose 9 and 2-deoxyglucose 10 were successfully synthesized and radiolabeled with [(99)mTc(CO)(3)(H2O)(3)](+) intermediate in high yield. The complexes were characterized by HPLC and its stability with histidine over time was challenged. Cell uptake and biodistribution studies in melanoma-bearing C57BL/6 mice were performed. Both compounds showed accumulation in tumor tissue with high tumor-to-muscle ratios. Thus, D-glucose- and D-2-deoxyglucose-Tc-99m complex could be considered as agents for melanoma diagnosis. (C) 2011 Elsevier Ltd. All rights reserved.
• JP5649073
  申请人：——

  公开号：——

  公开（公告）日：——
• A Sugar Decorated Macromolecular Bottle Brush by Carbohydrate-Initiated Cationic Ring-Opening Polymerization
  作者：Christine Weber、Justyna A. Czaplewska、Anja Baumgaertel、Esra Altuntas、Michael Gottschaldt、Richard Hoogenboom、Ulrich S. Schubert

  DOI：10.1021/ma202401x

  日期：2012.1.10

  The capability of a range of protected glucose- (Glc), galactose- (Gal), and fructose- (Fm) based tosylates and triflates to initiate the living cationic ring-opening polymerization of 2-ethy1-2-oxazoline (EtOx) was investigated by detailed kinetic studies utilizing H-1 and F-19 NMR spectroscopy and SEC as well as MALDI and ESI TOF mass spectrometry. The Glc and Gal tosylates and a sterically hindered Fm triflate revealed slow and incomplete initiation, whereas the Glc and Gal triflates resulted in living polymerizations. Well-defined Glc as well as Gal alpha-end-functionalized PEtOx was obtained after deprotection. Functionalization of the living oxazolinium chain ends with methacrylate anions resulted in a macromonomer that was applied for RAFT polymerization. Deprotection resulted in a comb polymer that is selectively functionalized with Glc at the ends of all side chains (DPbackbone = 13, DPside (chains) = 10, PDI = 1.11).